Journal
GREEN CHEMISTRY
Volume 16, Issue 3, Pages 1153-1157Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3gc42132e
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Funding
- Spanish Ministerio de Economia y Competitividad [CTQ2011-28512]
- Generalitat de Catalunya [2009SGR 00623]
- ICIQ Foundation
- ICREA Funding Source: Custom
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Unprotected indoles have been efficiently converted to enantiomerically enriched indolines (up to 91% ee) by a stepwise process: (reusable) Bronsted acid-mediated C=C isomerisation and asymmetric hydrogenation using enantioselective iridium catalysts derived from P-OP ligands. This straightforward combination of (reusable) Bronsted acids, which activate the indole ring for hydrogenation by breaking its aromaticity, and enantiomerically pure [Ir(P-OP)](+) complexes as hydrogenation catalysts affords the resulting indolines with high enantioselectivities.
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